CHEBI:10041 - withanolide D

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ChEBI Name withanolide D
ChEBI ID CHEBI:10041
Definition A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 22 (the 4β,5β,6β,22R stereoisomer). Isolated from Tubocapsicum anomalum and Withania somnifera, it exhibits cytotoxic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:66324
Supplier Information
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Formula C28H38O6
Net Charge 0
Average Mass 470.59770
Monoisotopic Mass 470.26684
InChI InChI=1S/C28H38O6/c1-14-12-22(33-24(31)15(14)2)27(5,32)19-7-6-17-16-13-23-28(34-23)21(30)9-8-20(29)26(28,4)18(16)10-11-25(17,19)3/h8-9,16-19,21-23,30,32H,6-7,10-13H2,1-5H3/t16-,17-,18-,19-,21-,22+,23+,25-,26-,27+,28+/m0/s1
InChIKey SASUFNRGCZMRFD-JCUIILOWSA-N
SMILES CC1=C(C)C(=O)O[C@H](C1)[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3C[C@H]4O[C@]44[C@@H](O)C=CC(=O)[C@]4(C)[C@H]3CC[C@]12C
Metabolite of Species Details
Withania somnifera (NCBI:txid126910) Found in leaf (BTO:0000713). See: DOI
Tubocapsicum anomalum (NCBI:txid180580) See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via withanolide )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing withanolide D (CHEBI:10041) has role antineoplastic agent (CHEBI:35610)
withanolide D (CHEBI:10041) is a δ-lactone (CHEBI:18946)
withanolide D (CHEBI:10041) is a 20-hydroxy steroid (CHEBI:36854)
withanolide D (CHEBI:10041) is a 4-hydroxy steroid (CHEBI:62846)
withanolide D (CHEBI:10041) is a enone (CHEBI:51689)
withanolide D (CHEBI:10041) is a epoxy steroid (CHEBI:145217)
withanolide D (CHEBI:10041) is a ergostanoid (CHEBI:50403)
withanolide D (CHEBI:10041) is a secondary alcohol (CHEBI:35681)
withanolide D (CHEBI:10041) is a tertiary alcohol (CHEBI:26878)
withanolide D (CHEBI:10041) is a withanolide (CHEBI:74716)
Incoming 17α-hydroxywithanolide D (CHEBI:66329) has functional parent withanolide D (CHEBI:10041)
IUPAC Name
(4β,5β,6β,22R)-4,20-dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione
Synonyms Sources
4β,20α-dihydroxy-1-oxo-5β,6β-epoxy-20S,22R-witha-2,24-dienolide ChEBI
Withanolide D KEGG COMPOUND
Manual Xrefs Databases
C00003677 KNApSAcK
C08842 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
30655-48-2 CAS Registry Number ChemIDplus
5173298 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
1125091 PubMed citation Europe PMC
17103214 PubMed citation Europe PMC
17417907 PubMed citation Europe PMC
20836852 PubMed citation Europe PMC
22479585 PubMed citation Europe PMC
22695853 PubMed citation Europe PMC
Last Modified
28 October 2019